Silver catalyzed zinc Barbier reaction of benzylic halides in water

被引：35

作者：

Bieber, LW ^{[1
]}

Storch, EC ^{[1
]}

Malvestiti, I ^{[1
]}

da Silva, MF ^{[1
]}

机构：

[1] Univ Fed Pernambuco, Dept Quim Fundamental, BR-50670901 Recife, PE, Brazil

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 51期

关键词：

Barbier reaction; silver catalysis; addition; dimerization; reduction;

D O I：

10.1016/S0040-4039(98)02199-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzylic chlorides react in aqueous dibasic potassium phosphate under silver catalysis with aromatic aldehydes in the presence of zinc dust to give 1,2-diaryl alcohols in moderate to good yields. Dimerization to bibenzyls and reduction of the halide are important side reactions. A wide range of substituted aromatic and heteroaromatic aldehydes and of substituted benzylic chlorides can be used. Aliphatic aldehydes and ketones are unreactive. A mechanism of two SET on the metal surface is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9393 / 9396

页数：4

共 14 条

[1] Reformatsky reaction in water: Evidence for a radical chain process
Bieber, LW
Malvestiti, I
Storch, EC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9061 - 9064
[2] 1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS
CHAN, TH
LI, CJ
LEE, MC
WEI, ZY
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05): : 1181 - 1192
[3] CROSSED ALDOL TYPE CONDENSATION-REACTIONS IN AQUEOUS-MEDIA
CHAN, TH
LI, CJ
WEI, ZY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) : 505 - 507
[4] Concerning a simple formation of stilbene, mono-4-meth-oxy-stilbene and alpha-methyl-stilbene.
Hell, C
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1904, 37 : 453 - 458
[5] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications
Li, CJ
[J]. TETRAHEDRON, 1996, 52 (16) : 5643 - 5668
[6] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION
LI, CJ
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2023 - 2035
[7] LUBINEAU A, 1994, SYNTHESIS-STUTTGART, P741
[8] ULTRASOUND IN ORGANIC-SYNTHESIS .16. OPTIMIZATION OF THE CONJUGATE ADDITIONS TO ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA
LUCHE, JL
ALLAVENA, C
[J]. TETRAHEDRON LETTERS, 1988, 29 (42) : 5369 - 5372
[9] MALVESTITI I, UNPUB
[10] ALLYLATION OF ALDEHYDES AND KETONES IN THE PRESENCE OF WATER BY ALLYLIC BROMIDES, METALLIC TIN, AND ALUMINUM
NOKAMI, J
OTERA, J
SUDO, T
OKAWARA, R
[J]. ORGANOMETALLICS, 1983, 2 (01) : 191 - 193

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